


Black Sunsets on the Sky and I'm Thinking

by waitingforjudas



Series: Judas' Kinktober 2019 [20]
Category: Supernatural
Genre: Alpha Castiel/Omega Dean Winchester, Alpha/Beta/Omega Dynamics, Alternate Universe - Human, Dialogue Heavy, Dirty Talk, In This House We Hate John Winchester, Internalized Homophobia, John Winchester's A+ Parenting, Kinktober, Kinktober 2019, M/M, Masturbation, Phone Sex, Roleplay, Sex Work, Sex Worker Castiel (Supernatural), Sexual Roleplay, Top Castiel/Bottom Dean Winchester, a/b/o is part of a roleplay
Language: English
Status: Completed
Published: 2019-10-21
Updated: 2019-10-21
Packaged: 2020-12-31 08:00:22
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,808
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21123179
Author URL: https://archiveofourown.org/users/waitingforjudas/pseuds/waitingforjudas
Summary: Dean wants to relax with anybody other than his right hand. But lately, he’s started to want to maybe… be with a man, even though there’s no way that he could trust anybody enough to do that.But surely calling into a phone sex line would be a safe way to try it out.Written for Kinktober 2019 prompts: Sex Work, Masturbation, and Roleplay.





	Black Sunsets on the Sky and I'm Thinking

**Author's Note:**

> I actually finished this 12 hours ago and then thought I had posted it but I didn't and all I can blame is the cocktail of medications I'm on. 
> 
> Also, no, I have never called into a phone sex line. I would assume that they would take payment information before connecting a caller, but that sounds boring as shit to read about, so suspend your disbelief, friends. 
> 
>   
_Written for Kinktober 2019. Prompt list can be found at https://twitter.com/NihilistShiro/status/1162794889970511872._

Dean pulled out his duffel bag and carefully unzipped the inner pocket. He hadn’t gotten to spend much time by himself lately—by lately, he meant for over a month—and it was wearing on him. For whatever reason, there had been case after case after case, and they just kept coming. 

But now? Sam had finally left him alone, but that was only because Dean had claimed that he had a killer headache. 

He was getting one, anyway. 

He’d cooked up this plan a couple weeks into his month of complete celibacy, when all he’d had over the past week and a half had been a hurried session in the shower with his right hand and a pump of hotel conditioner that had made his dick break out in a rash. 

He would fake a headache, get out every last toy and lube he owned—and, in the weeks leading up to this, had found a couple different things to try with the very limited free time he had—and then he would bar the doors, salt the windows, pray Sam didn’t come back earlier than the hour he’d said the library research would take, and call a phone sex line. 

The last part of the plan was freaking Dean out a little. Because—well, he kind of had this fantasy that he’d never tried with anybody. It wasn’t even for lack of trying; it was just for lack of _trust_. Dean wasn’t exactly rearing at the chance to let some random Joe stick his dick in him, as much as he thought he’d enjoy it. 

But this was a phone call. That would be different. 

He could do a phone call. The worst that could happen was—

Well, there were a lot of worst-case scenarios, and all of them were possible. 

Dean sighed, tossing the toys onto his bed. If it went bad, it was his own cell phone bill. And it wasn’t like the number wouldn’t get canceled within a couple months, anyway, once the credit card he was using got caught. 

If he was smart, he’d be using a prepaid phone, but Sam had insisted that the migration to smartphones was worth it if only because they could look things up on the go, or send pictures of crime scenes to each other. “And,” he’d said, “it has _mobile hotspot_. That means wherever we go, we always have Wi-Fi.”

It had been worth agreeing just to shut him up. 

Dean was stalling. He recognized that. He did. He just—the—

Dean turned on the alarms he’d set—ten minutes before Sam was due back, then three—and dialed the number from his contacts. 

“Welcome to Heavenly Voices. To continue your call in English, please press one. To continue in Spanish— For a female operator, press one. For a male operator, press two.” 

Dean pressed two, stomach flipping. 

“At the beep, please state your name.”

It beeped and Dean, on instinct, said, “Dean.” Then kicked himself, because he wasn’t supposed to give his real name, right? Or was that for the operator?

“Your name was recorded as _Dean_.” Dean winced at his voice over the line. “To re-record, press nine. To continue, press one. At the beep, please state your fantasy.”

“Um. Getting fucked?”

“Press one for the next available operator, or press two to enter an operator’s number at the prompt.”

Dean pressed one and waited. 

“Your estimated wait time is—”

“Hello, Dean,” a rich, thick, _deep_ male voice said. 

Dean shuddered and blushed. “H—Hi. Hey.”

“I hear you’d like to get fucked. Is that true?”

He nodded and kicked himself mentally. “Yes, it is.”

“My name’s Steve,” Steve said conversationally. “Why don’t you tell me a little more of what you’d like?”

Dean licked his lips. “Well, uh… I’m… in heat?”

“Are you, omega?” Steve asked and Dean had to suppress a relieved sigh. Thank God Steve hadn’t needed an explanation. 

“Yes, alpha,” Dean whispered. “I’m—I’m so wet.”

“For me.” Steve sounded almost amused, unconcerned, and Dean whimpered. 

“_Yes_,” Dean hissed. 

“I’m sorry I’m out of town, little omega,” Steve said, “but I know you’ll be all right. I’ll book a flight home now. Do you have your toys?”

“Y—Yeah. I do.”

“Which ones?”

“Um, the—the nipple clamps. And the beads, and the vi—vibe. And the, um. The… the dildo. With the knot.” The last few words came out barely above a whisper and Dean cringed, waiting for Steve to kick him off the line. 

“Good omega, aren’t you,” Steve said. 

Dean relaxed against the headboard. “Thank you, alpha.”

“Get the vibrator first. Tell me about it, how good it’ll make you feel.” 

Dean lunged forward, almost dropping the phone in his haste to grab the vibrator and tell Steve about it. “Shit,” he muttered. 

“Put me on speakerphone, Dean. You’re going to need your hands free, anyway.”

“Yes, alpha.” Dean set it to speakerphone. “Okay, it’s on speaker.”

“Tell me about your vibrator. Is it long or short? Where do you like using it?” 

“It’s, um. It’s a bullet.”

“Dean, you didn’t answer my other question.” 

Dean flushed. “Um….”

“Omega, you’re in heat. You need your alpha to help you, don’t you?”

“I do.”

“That’s right, isn’t it? You wouldn’t have called otherwise. Tell me, _omega_, where you like teasing yourself with that little vibe.”

“My… my….”

“I bet it’s your nipples,” Steve said, and Dean moaned, nodding. “Am I right, omega?”

“_Yes_, alpha.” His stomach was flipping with excitement—he could barely hold himself together, hardly stop himself from just flicking the vibrator on and teasing himself. It almost felt like he was actually in heat, not just pretending. 

“Do you want to come, omega?”

“So bad, alpha. _Please_.”

“I think I like hearing you beg, Dean. Get your nipple clamps.”

Dean whined but obeyed. He wanted to please his alpha, he really did. “If I do,” Dean said, as if he didn’t already have them in hand, wasn’t already opening and closing them, fidgeting with them, “will you breed me?”

Steve was silent for a moment and then he groaned. “Shit, _Dean_. Yes, yes, of course I’ll breed you. I’ll breed you full of my come and my pups, mark you up and claim you as mine. Maybe I’ll even bite you again, freshen up my mating mark.”

Dean moaned, unable to even put words together coherently. “_Alpha_.”

“Put a clamp on your right nipple,” Steve said, and Dean did. “How does it feel?”

“Good,” Dean murmured. 

“Put on the other one, then.”

“It’s— Alpha, it’s so good. Please—please, more. It hurts.”

Steve chuckled, low and dark, and Dean’s stomach flipped. 

This was better than he could have even dreamed. 

“I know, baby,” Steve said, and Dean relaxed so suddenly that he realized he’d been tense the whole time. Probably since he’d dialed the line in the first place. “I know. Turn on your vibrator, omega.”

“Can—can you call me—maybe….”

“I won’t judge you,” Steve murmured, and Dean nodded and licked his lips.

“Baby. Can you call me—”

“Of course, baby,” Steve said, the word sounding fucking _filthy_ on his tongue. “Is your vibrator on, baby?”

“Yeah. Yeah.”

“Where do you think I want you to use it?”

“My—my nipples.” 

“That’s right.” He sounded so genuinely proud that Dean couldn’t help but preen a little. “That’s exactly right, baby. Use it on top of the clamps—make your nipples so sensitive that if you took off the clamps, you’d shoot your omega load everywhere. Give the alphas a run for their money.”

Dean shivered. “O-Okay, alpha.”

“Good.” Steve groaned again. “Let me hear every noise you make, baby. I need to make sure you’re enjoying this, that it’s helping your heat.”

“Yes, alpha.” Dean sucked in a sharp breath the moment the vibrator touched the first clamp. “Oh—shit, Steve.” His breaths were more of whimpering, breathy moans, but he couldn’t find it in himself to be embarrassed about it. Much, anyway. 

“Shit, baby,” Steve said, “you sound so pretty. So needy. Is your hole wanting more attention?”

“_Alpha_,” Dean cried out, arching off the bed. 

“Did you come, baby?” Steve sounded—professional. Detached, almost, but— Dean knew how to read people. He picked up on their tics fast, and it was half of what made him the lead on questioning people. 

He sounded almost disappointed. 

“Not yet, alpha,” Dean said, every word carefully enunciated. 

“Good,” Steve murmured, and then, louder, “You can, baby. Any time you need.”

“I know,” Dean said, blushing and ducking his head. “I just—I wanted to come with you.”

Steve grunted. 

It didn’t sound fake. 

“That’s— Shit, Dean. Okay. You—you should do that. Shit. Where were we?”

Dean grinned lazily. “You were saying my ass needed more attention.”

“That’s right,” Steve said. “I think it does, Dean.”

“What do you want me to do, alpha?”

“Cas,” Steve said. 

Dean hesitated. “I— What?”

“My name. It’s Cas.”

“Cas,” Dean said slowly, smiling around it. “I like that. It suits you. Unusual name, unusual voice.” 

Cas chuckled. “Maybe. Now, you said that you had some beads, didn’t you, baby?”

“Yeah.”

“I assume you have some lube. You’re still in early heat, aren’t you? Not quite wet enough to work everything into your hole with your natural slick.”

Dean nodded. “Yeah, yeah, I—I have lube.”

“Slick yourself up a little more. I want to hear the beads going in your ass.” 

Dean sucked in a sharp breath. “Okay. Yeah, I can do that, Cas.”

He heard some rustling over the line and then Cas moaned. “I said slick yourself up, Dean.”

Dean grabbed the lube and squirted some out onto his fingers. “How—how many fingers do you want me to use, Cas?”

“Go slow,” Cas said, voice dropping somehow _lower_. “One finger. Tease yourself.”

Dean glanced at the clock. “I—I can’t. My brother’s going to be back in twenty minutes and I need a few minutes to put everything up.”

“That’s fine,” Cas said. “One finger, and you’ll move a little faster. Okay?”

“Okay,” Dean mumbled. 

“Hey— What was that?”

“What?” Dean tried not to go on total high alert, but that phrase—_what was that?_—was generally a warning that things were about to get bad. 

Really bad. 

“What was that disappointment for?”

Dean shrugged. “I don’t know.”

“You can tell me.”

“I don’t— I don’t know. I’m in my thirties and I’ve never been with a guy and now the only time that I have a chance, it’s just—”

“Hold on for a moment,” Cas said, and Dean deflated. 

“Yeah, of course. I’m sorry. Sorry.”

The line went quiet, but not dead, and Dean stared down at himself. His cock was throbbing, the veins standing out on his skin, and his hand was covered in lube, and he was fucking pretending to be an omega just so that having fucking phone sex with a man would seem a little more palat—

“Dean? Hello. I want you to get a pen and paper.”

Dean glanced around and spotted a cheap motel notepad with probably four sheets of paper left and a pen that was almost certainly nearly dry. “Okay.”

“Write down ‘Castiel.’ C-A-S-T-I-E-L.”

Dean frowned, but did it. “Okay, I wrote it.”

“Then 555-0182.”

Dean froze. “Are you—are you giving me your number?”

“Yes.”

Dean’s eyebrows rose. “Really?”

“555-0182. It’s my private cell phone.”

“Yeah, no, no, I got—I got that.”

“Did you write it down?”

“Can you—” Dean reddened, wiping the lube off the pen. “Can you repeat it? One more time.”

Cas—_Castiel_—did, and Dean wrote it down. 

“You just gave me your number.”

“My new number, omega. I’m sorry I didn’t get it to you sooner.” Cas had slipped right back into the fantasy, and Dean just followed him without hesitation. 

“Thank you, alpha,” he whispered. “Can I— Will you please fuck my ass now?”

“Your tight little hole? Are you sure you’ve prepped enough?” 

Dean snickered a little. “No, I don’t think so.”

“Well, baby, then I think you need to open yourself up a little more. Why don’t you start with two fingers? I know how desperate you are.”

Dean swallowed and slicked up his fingers again, coating them in lube. “Okay. Two?”

“It’s okay if you don’t want to—”

Dean plunged two fingers inside of himself—his ring and pinky fingers. He was aware it might not have been the best decision on the planet, but he just felt full. 

So fucking full—and it was probably for the best that Cas was making him go slow. 

“Shit—Dean—”

He realized that he was letting out this long, low, keening whine, and blushed, trying to cut it off. 

“Don’t you dare stop,” Cas snarled, and Dean moaned. 

“_Alpha, please_ breed me. _Please_ fuck me.”

“Once you’re loose enough.”

“I am!”

He wasn’t.

“Humor me, baby,” Cas said, but it was kind. 

Dean would do anything Cas asked, as long as he said it like that. “Okay.”

“Add some more lube. My knot’s going to be hard for you to take unless you’re open enough.”

“I know,” Dean murmured, foregoing pulling his fingers out and instead just scissoring them open and squirting lube directly into his hole as he groaned, toes curling into the sheets, pressing up on the balls of his feet. “God—_Cas_.”

“Feels good?”

“I just—I’m so wet for you.”

“I’m so hard for you,” Cas said, and swore, and Dean paused. 

“Are you actually touching yourself?”

“Can I text you something?”

Dean shrugged. “You don’t have my number.”

“Right. Shit. I— Yes. Yes, I am. I was going to send you a picture, but I am.”

“Oh, God—” Dean rattled off his number. “Text it. Text it, Cas.”

“Okay,” Cas said, chuckling, and then Dean’s phone was lighting up with the most gorgeous cock he’d ever seen. 

“Do you moonlight as a porn star?” Dean stared at it, the thickness of it—the fucking Pringles can next to it for scale. “God, Cas, I want you in me. Now. _Now_.”

“Fuck, baby. Okay. But you’re gonna take my knot slow, and you’re gonna ride me, control all of the pace yourself. Understand?” 

“Yeah— Yes, alpha, I understand.”

“Good. Slick up my cock, baby.”

Dean scrambled to grab the dildo and squirt lube onto it. A little—a lot—more came out than he was expecting and he tried to stifle a snort. “Sorry, I just— It’s a little more lube than— I—”

“It’s gonna feel so good in you, though, isn’t it, baby? And I’ll hear you riding it, fucking my cock, hole gripping it. I’ll hear how wet you are, how much wetter you get taking my cock.”

Dean tightened his hold on his dick. “Cas—Cas, it’s not even in me yet. I’m gonna shoot too fast.”

“Take it, Dean.” 

So he did, lining up the dildo to his asshole and breathing out and bearing down as he took it down to the knot. 

“Dean, I’m— I’m gonna come soon.”

He was already too close just taking the cock. “So’m I. Do it, Cas. Fill me with your come.”

“Gonna—_shit_—gonna knot you, Dean.”

“Tell me when it hits.”

“It’s— It’s— Dean!”

Dean dropped down onto the knot, working to take the whole thing inside of him. 

It was _brutal_ pressing on his prostate, but he still couldn’t come. 

“I— Cas, I can’t— I—” Dean broke off into a sob, desperation overtaking him suddenly. 

“Come for me,” Cas said, and he sounded absolutely _wrecked_. “Take off your nipple clamps, both of them, and come for me.” 

Dean fumbled with the clamps, hands heavy and not cooperating, and then he managed to get his fingers on them and he squeezed and then blood _rushed_ into them and the knot was on his prostate and he rocked, just a little, and then he was coming, thick and heavy, all over his sheets, all over his stomach, all over _everything_, and he was vaguely aware that Cas was talking to him, but he just kept coming for what felt like eternity until he just collapsed. 

He just fucking collapsed onto the bed, the dildo’s knot having come out enough that the knot slid the rest of the way out. 

“Dean. Dean, I need you to talk to me. Are you okay?”

“I’m fine,” Dean said, blinking up at the ceiling and then managing to—slowly—pick up his phone and switch Castiel off of speakerphone. “I’m good.”

“Okay, Dean. I’m going to hang up so you can clean up before your brother gets back. You can call or text me if you need anything. Or, um, if you want to talk again.”

Dean grinned. “I would fucking _love_ that, Cas.”

**Author's Note:**

> If you enjoyed, please consider leaving kudos or a comment. 
> 
> _This work was inspired by @NihilistShiro's Kinktober prompt list, available here: https://twitter.com/NihilistShiro/status/1162794889970511872 _


End file.
